What It Means to Be an Effective Leader in Times of Change


The challenges of being a leader are plentiful, and it seems like each year presents a new set of difficulties. Competition, revenue growth, and change management are just a few hardships that can easily test the fortitude of even the most seasoned leaders — especially during trying times.

But the insurance and financial services sector is highly adaptable. Professionals at all levels have found ways to remain flexible, productive, self-motivated, and collaborative. It’s a true testament to the traits of the industry’s workforce. It’s also a true testament to our leadership teams and their ability to lead through uncertainty.


In June 2020, the PIMA conference on leadership covered many of the challenges of being a leader during times of great change; leading remote and virtual teams was a major theme.

This has long been a struggle in the insurance industry, and our speakers — all successful leaders — delved deeper into the subject matter to help others in the industry maneuver new circumstances and find actionable solutions to leadership challenges. The following are some of the insights on how to lead remote teams presented at the PIMA conference session “Leading & Engaging a Remote Workforce”:

  • Increasing employee engagement.

“It was important for us to step up employee engagement using daily check-ins with team members and making sure we’re giving employees ample time to talk about what’s going on in their personal life and the challenges they’re having at work.”

~ Avery Smith, president of Kelsey National Corporation

  • Improving transparency.

“We send surveys out each week via Officevibe with a few questions, and we’re getting real-time feedback that helps us with our weekly communication.”

~ Chris Burke, president and CEO of AGIA Affinity

  • Investing in technology.

“We’re taking a step back and looking at how we can better serve the market with the tools we have.”

~ Bill Suneson, co-founder and CEO of Bindable

  • Stressing adaptability.

“Remote call centers are not only possible but also are a new competitive call for talent. We haven’t missed a step in productivity, service standards, and deadlines for projects.”

~ Chris Burke, president and CEO of AGIA Affinity

  • Managing priorities.

“There is a tendency as leaders to focus on the ‘what,’ but we need to focus on the good things employees have done.”

~ Avery Smith, president of Kelsey National Corporation

During times of uncertainty, businesses need more hands-on leadership. Find your clarity of vision, and then use it to lead with intent, own the situation, and arrive at creative ways to inspire, motivate, and face the challenges of leading a remote team. Be upfront about obstacles, and remove barriers whenever possible. During adjustment periods, the responsibility rests on leaders to make it a little easier for their teams.



Most leaders have experience working with a remote workforce, but the pandemic emphasized how important it is to communicate effectively to stay connected with a dispersed team.

Here are a few engagement and communication tips for working remotely from PIMA members:

  • Daily check-ins with team members.
  • Weekly video updates.
  • Phone calls instead of lengthy emails.
  • Encouraging employees to “unplug” from work.
  • Technology training to ensure connectivity.
  • Wellness programs to promote employee health.

Learning how to stay connected with employees has a lot to do with frequency. But even more so, it’s about engaging in meaningful conversations — which often requires leaders to overcome the common barriers to effective listening.

If you’ve read Stephen Covey’s “The 7 Habits of Highly Effective People,” you already know some of the most common barriers to effective listening. You also recall the five levels of listening. For those who haven’t read the book, here’s an overview:


What Are the Five Levels of Listening?

  1. Ignoring. Just as it sounds, ignoring happens when someone tunes out of the conversation. For example, this might happen on a virtual call when someone’s eyes gradually turn away from the screen — and his or her attention drifts toward something other than the discussion at hand.
  2. Pretending.Probably the most common barrier to effective listening, pretending happens when you acknowledge someone is talking (by nodding or giving an “uh-huh”), but your face tells a different story.
  3. Selective. Selective listening is what confident people tend to employ, as there’s an assumption that they already know what the other person is going to say. They tune in and out of conversations, so they end up missing key elements.
  4. Attentive. At this level, you’re starting to get close to being an effective listener. The mind processes the conversation but still forms a response at the same time.
  5. Empathetic. This is where you’re truly being an effective listener. You’re actually curious and give full attention to what the person is saying — without jumping to conclusions.

Of course, being an effective listener is only part of the equation for how to stay connected with employees who are remote. There are a number of other factors at play when trying to connect and communicate with someone in another space.

For many PIMA members, a curiosity-first approach has proven beneficial in remote work communication. The key is entering into any given discussion by understanding that you don’t know what you don’t know. According to the June PIMA conference keynote speaker, Sarah Noll Wilson, this approach can be summed up in three words: explore, experiment, and examine.

  • Explore —Make observations, share your interpretations, and invite other perspectives.
  • Experiment — Test assumptions, change purposefully, and regulate the heat.
  • Examine — What do you hold on to? What do you let go of? What do you transform?


Working with a remote team, as mentioned, poses significant challenges for leaders. You’re not in the same space, making collaboration a problem. Follow these three steps to promote greater remote work team collaboration:

  1. Engage. Sometimes, keeping remote teams engaged and happy is as simple as being present as a leader. Stay in contact with employees. Make sure everyone is part of conversations, and give your team the tools necessary to succeed.
  2. Recognize. Just because a team is working remotely doesn’t mean you should stop acknowledging everyone’s contributions. Make a habit of publicly recognizing team members’ accomplishments. Consider commenting on their productivity and outcomes on a week-to-week basis.
  3. Provide a platform. Employees need a means of collaborating and communicating with leadership and their colleagues. Invest in the best technology for working remotely, including real-time chat tools (Slack), video call platforms (Zoom, Cisco Webex), project management software (Trello, Basecamp), and brainstorming/visual collaboration digital workspaces (MURAL, Lucidchart). It’s all about finding what works best for your organization. Test a few out, and then commit to whichever ones check all the boxes for remote working technology.



For better or worse, work-life balance for employees is more of an illusion than anything else. Today, it’s really about finding a work-life integration that seamlessly blends the two parts of your day-to-day.

This, of course, doesn’t mean employees shouldn’t strive to strike a balance between their personal and professional pursuits. It’s healthy to remove yourself from work, but this can be especially difficult for remote employees. It’s often up to leaders to help guide their employees in finding a good work-life balance.

Here are a few ways to create a better work-life balance for your employees — and yourself:

  • Set appropriate goals and expectations from the very start.
  • Only schedule meetings during normal work hours.
  • Communicate only when employees are “on the clock.”
  • Encourage remote workers to take breaks (software to set reminders is available).
  • Focus on outcomes rather than hours — it’s much more goal-oriented.
  • Make “out of office” notifications mandatory.
  • Don’t incentivize 24/7 engagement.

While work-life balance for employees may be a fallacy at the moment, it doesn’t mean business leaders are absolved of their responsibility. Employees will always take their cues from the company higher-ups.

Take the extra effort by creating policies around best practices for working remotely. You want to encourage structure, establish routines, and offer a sense of separation within the new work environment.



Being vulnerable at work can be uncomfortable. It’s often seen as a sign of weakness, so people in leadership roles usually consider it a liability and shy away from sharing vulnerable parts of themselves. But vulnerability-based leadership is critical, especially in times of change. It’s the ultimate act of showing up and connecting with your team.

Learning how to show vulnerability as a leader can take some work. The work is worth it, however, as being vulnerable at work can lead to greater trust and respect from your team. It also gives everyone more room to make mistakes, which can certainly help with innovation and change.

So, let’s take a moment to explore vulnerability-based leadership and what it could do for your organization. In no particular order, here are four ways to show vulnerability as a leader:

  1. Share. Set mental boundaries of what you will and will not share before you begin practicing vulnerability-based leadership. You don’t need to disclose your deepest, darkest fears, but you should be willing to expose certain facets of your life with the people you lead and work beside.
  2. Take a back seat. Sometimes, it’s important to let other people drive the conversation. Observe and step in when necessary, but taking a back seat allows employees to feel more connected with one another. It also helps them feel like they’re being heard, which can strengthen their commitment to the organization as a whole.
  3. Get rid of your ego. You may have the answer to a question, but wouldn’t it be more beneficial to let a team member reach his or her own conclusion? Let employees take the lead by turning the question around and allowing them to work through the situation at hand.
  4. Let go. Letting go doesn’t mean abandoning your team. With vulnerability-based leadership, you bring more of your “self” to work, which allows everyone else to do the same. You’re then setting the stage for team members to build stronger relationships and develop greater loyalty to your organization.



The coronavirus pandemic has certainly been one of the biggest challenges facing leaders today, but it isn’t the only hurdle industry leaders must overcome. Social change and calls for diversity are also emerging issues in leadership — and for a good reason.

Policies for diversity in the workplace do more than create an inclusive environment. Research shows that diverse teams make better business decisions up to 87% of the time. They also arrive at decisions two times faster and with half as many meetings. Another study revealed that inclusive companies generate 2.3 times more cash flow per employee and 1.4 times more revenue. It shouldn’t come as a shock that inclusive teams are 120% more capable of meeting financial goals.

Beyond that, embracing diversity in the workplace can lead to higher employee engagement, retention, and morale — not to mention improved company image, which can do wonders for your recruitment efforts. The list of benefits of equality, diversity, and inclusion in the workplace goes on and on.

The question then becomes a bit more focused:


What Is Diversity and Inclusion in the Workplace?

Diversity and inclusion can mean a number of things. But when it comes to the workplace, it often refers to the mission, strategies, and practices used to empower people of different ages, genders, ethnicities, sexual orientations, and national origins — among other factors.

Policies for diversity in the workplace can include:

  • Representation of diversity at all levels of an organization.
    • Representation of diversity among all stakeholders (internal and external).
    • Diversity and inclusivity training.
    • Equal access to opportunities.
    • Fair treatment of all employees and customers.
    • Collaborative conflict-resolution processes.
    • Teamwork and collaboration among employees.
  • Hiring a chief diversity/equality officer.

The benefits of equality, diversity, and inclusion in the workplace cannot be overstated. When leaders embrace diversity in the workplace, they open the entire organization to a variety of perspectives and viewpoints, which can only help increase creativity, innovation, and profits. However, creating policies for diversity in the workplace is still one of the biggest challenges facing leaders today. It will take a concerted effort to enact the necessary change.



Leading a team through change can be a struggle for even the most seasoned professionals — especially when daily routines fall to the wayside and “business as usual” is no more.

PIMA membership can help. You and your team can gain access to PIMA continuing education opportunities through an extensive library of industry-specific articles, whitepapers, case studies, and more. You also have a chance to engage in conversations through our online portal, which connects you to more than 500 leaders in the insurance and financial services industry.

PIMA has many avenues for learning, knowledge sharing, and building peer-to-peer network connections. To learn more about how a PIMA membership can help you overcome the challenges of being a leader today to lead your team into a promising future, contact us.

Published on October 26, 2020.

PIMA® (Professional Insurance Marketing Association®) is a member-driven trade association focused exclusively on the group-sponsored benefits market.